The structural formula: ##STR1## represents N-methyl-3 R-(2-methylphenoxy)-3-phenylpropylamine when R.sup.r is methyl, and represents N-methyl-3 R-(2-methylthiophenoxy)-3-phenylpropylamine, when R.sup.r is methylthio. Both N-methyl-3 R-(2-methylphenoxy)-3-phenylpropylamine and N-methyl-3 R-(2-methylthiophenoxy)-3-phenylpropylamine act as selective and potent inhibitors of norepinephrine uptake.
Syntheses of N-methyl-3 R-(2-methylphenoxy)-3-phenylpropylamine are described in U.S. Pat. Nos. 4,018,895, 4,194,009, 4,314,081 and 4,777,291, the disclosures of which are hereby incorporated by reference. A synthesis of N-methyl-3 R-(2-methylthiophenoxy)-3-phenylpropylamine is described in U.S. Pat. No. 5,281,624, the disclosure of which is hereby incorporated by reference.
The structural formula: ##STR2## represents N-methyl-3 R-(4-trifuoromethylphenoxy)-3-phenylpropylamine, (R)-fluoxetine.
Syntheses of (R)-fluoxetine, (R)-N-methyl-3-(4-trifluoromethylphenoxy)-3-phenylpropylamine, are known in the art and taught in U.S. Pat. No. 5,708,035.
In known syntheses of these compounds either a mixture comprising both the R and S enantiomers of the desired compound is formed and then the desired enantiomer is separated from the mixture using techniques known in the art or the desired enatiomer is prepared directly from a chiral substrate. It is desirable to develop an alternate process that allows for making of the individual enantiomers directly.